Synthesis and antiviral activity of 3'-heterocyclic substituted 3'-deoxythymidines.
Various 3'-deoxythymidine analogues with an heterocyclic five-membered ring in the 3'-erythro position have been synthesized. The pyrrol-1-yl (3) and the 1,2,4-triazol-4-yl (5) compounds were synthesized from 1-(3-amino-2,3-dideoxy-beta-D-erythro-pentofuranosyl)thymine. The pyrazol-1-yl (16a), imidazol-1-yl (16b), and 1,2,4-triazol-1-yl (16c) derivatives were obtained by epoxide opening of the corresponding 1-(2,3-anhydro-beta-D-lyxofuranosyl)thymines followed by 2'-deoxygenation. Only the 3'-pyrrol-1-yl derivative showed marginal antiviral activity against human immunodeficiency virus.
Wigerinck
P
P
Rega Institute for Medical Research, Katholieke Universiteit Leuven, Belgium.
Van Aerschot
A
A
Janssen
G
G
Claes
P
P
Balzarini
J
J
De Clercq
E
E
Herdewijn
P
P
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis*; D002472:Cell Transformation, Viral / Q000187:drug effects; D002478:Cells, Cultured; D055598:Chemical Phenomena; D002621:Chemistry; D003588:Cytopathogenic Effect, Viral / Q000187:drug effects; D006678:HIV / Q000187:drug effects; D006801:Humans; D066298:In Vitro Techniques; D051379:Mice; D013329:Structure-Activity Relationship; D013936:Thymidine / Q000031:analogs & derivatives*; D014779:Virus Replication / Q000187:drug effects
D000998:Antiviral Agents; D013936:Thymidine